01 of 08
Make Multiple Requests
With one exception, I have never received free room upgrades without making inquiries. The more you ask, the better your chances become.
Don't kid yourself: those chances are fairly slim, whether you're asking at the Trump International Hotel and Tower in Chicago or a well-worn four-star hotel in a smaller city. But at times, persistence pays off.
Don't confuse persistence with pestering. Asking 21 times and annoying everyone from the hotel operator to the general manager is neither good strategy nor proper manners.
However, there are three occasions when a polite inquiry about upgrade opportunities can be effective.
The first should be made when you make the reservation. The second inquiry comes when you confirm your stay with the hotel a day or two before arrival. The third should come at check-in.
By the time you walk up to the desk, they know you want free room upgrades and that you've been persistent but not obnoxious. You're a realistic budget traveler. Click "next" and consider that realism in a different context.Continue to 2 of 8 below.
02 of 08
Shoot for a Realistic Goal
The photograph above was taken in a four-star Milan hotel. On arrival, I received a free room upgrade without asking for it. In fact, this room was secured with a Priceline bid.
The hotel was not busy that day, and we were staying for only one night. After hearing about the upgrade, we wished we had booked for two or three nights.
But would we have received this room upgrade on a three-night stay? Probably not.
When you shoot for anl upgrade, you must realize that longer stays will decrease your odds of success. It probably wasn't possible for the hotel to sell this beautiful Milan suite on the night of our arrival, but over the course of three days, they probably would have had someone willing to pay for it. So be realistic: ask for free room upgrades on short stays.
Click "next" and consider another important goal: flexibility.Continue to 3 of 8 below.
03 of 08
Have a Flexible Schedule
Budget travelers with flexible schedules get all the perks. They score the last-second discounts on cruise cabins, flight deals and resort stays. They're also more likely to pick up free room upgrades at that convenient downtown property.
If you develop a good relationship with management that is essential to these upgrades, you might learn that the night of your arrival is busy and an upgrade is highly unlikely. But if management says something like "too bad you're not coming that next week," are you ready to change your plans?
Obviously, there are many times when travel dates are not entirely of our choosing. But if you have the luxury of flexible travel plans, point out in one of your requests that if your proposed dates don't work, you're willing to consider alternate dates.
Click "next" and read more about how to arrange that flexible schedule.Continue to 4 of 8 below.
04 of 08
Off-Peak and Weekday Upgrades
Free room upgrades are more likely to occur when there are lots of empty rooms. Choose a date of arrival that increases your odds of success.
Think through this: off-peak days are best. If there is an event in the area that creates high demand for hotel rooms, you are going to be turned down for a room upgrade.
Think about weekdays and weekends, too. In resort locations such as the one you see pictured, you might find weekdays are the perfect time to make your request, as many travelers book three-day weekends. At this resort in the heart of Panama, summer months are also off-peak times for a visit.
At a downtown hotel that caters to business travelers, the opposite might be true. Lots of empty rooms are possible on weekends, but during the week those expense-account road warriors are filling every available room.
If you help a manager fill empty rooms at off-peak times, you begin to create good will that can be rewarded. Click "next" and read more.Continue to 5 of 8 below.
05 of 08
Positive Contacts with Hotel
What makes hotel managers happy?
The most obvious answer is a "no vacancy" sign out front. But there are other aspects of the hotel business that are important.
Positive feedback from a good stay that can be forwarded to the company's top management is always a valuable commodity. Hotel reviews posted on social media sites have a similar effect.
Let me be clear: I am not suggesting you flatter someone who doesn't deserve it. Don't trade a phony positive review for future free room upgrades.
But if you enjoy your stay, let someone know in writing. Tell them you'll be staying in the area again and you're likely to come back for another visit. Such feedback is greatly appreciated. Many times, managers see mostly negative comments, because happy people tend to leave quietly. Your note could stand out and make a positive impression.
Does the hotel have a loyalty program? If so, join it. It usually costs nothing and it signals you're interested in becoming a regular patron. As with frequent fliers in the air travel industry, hotel frequent guests are valued and sometimes rewarded.
Click "next" and consider what type of room you should consider.Continue to 6 of 8 below.
06 of 08
Book Mid-Range Rooms
Booking a mid-range room at a four-star property increases your upgrade chances.
That statement might not go over too well with budget travelers, who usually seek out the least expensive room and also sidestep extra hotel charges. It's a fine strategy that adds value to your trip, but you could fall to the back of the upgrade line.
If you are in hotel management and searching for a guest to upgrade, are you going to choose someone who made a Priceline booking or went for a small room? Or are you going to begin your consideration with mid-range room reservations?
This is a guideline rather than a rule. As I said, I once was upgraded to a suite on a Priceline reservation. It happens. But booking a mid-range suite will increase your chances of being upgraded to the penthouse.
Click "next" and consider the best times for check-in.Continue to 7 of 8 below.
07 of 08
Check In Later, But Not Too Late
Many hotels will allow new guests to check in as early as 3 p.m. It can be a great convenience.
But you are approaching the front desk for a free room upgrade. At that early hour, they might not yet have a clear picture of that particular evening's bookings.
People show up late or not at all. Guests with changing plans will walk in looking for a room. At 3 p.m., there is still some uncertainty on most nights.
Waiting a few hours before making your entrance is a better idea. You'll be making your third and final request for a free room upgrade. By early evening, management will be in a better position to make the call.
Important: don't wait too late. Sometimes the hotel manager goes home for the evening, leaving an assistant to make decisions. That person might not be authorized to upgrade you, and they're unlikely to call the manager at home for permission.
Click "next" and consider more about the human nature of this request.Continue to 8 of 8 below.
08 of 08
The picture above was taken in a premium suite inside the Sofitel St. James, one of the finest hotels in London. Heads of state and star entertainers have spent the night here. Gaining a free room upgrade to a suite such as this will be difficult, if not nearly impossible.
But you're determined to try. Just make sure your determination is cloaked in courtesy.
Hotel personnel are trained to be professional and even unemotional in their dealings with guests. But don't kid yourself. They are human and they don't enjoy dealing with difficult people any more than you do.
The reason they receive this training is that travelers under stress tend to be blunt and even rude. Hotel desk clerks absorb a fair amount of abuse, as do the hotel managers who must ultimately deal with these situations. As travelers, we all instinctively bellow "I want to speak to the manager" when things aren't going well.
So put a smile on your face and be on your best behavior when asking for free room upgrades. If your request is denied, keep smiling and don't blame the person who just ended the opportunity. Chances are good that he or she had little to do with the final decision. Instead, treat people behind the desk with courtesy. It is the right thing to do, and you never know how it might pay off later in the evening when a suite does become available and your kindness is still fresh on the mind of that clerk.